The overwhelming majority of criminal convictions occurs by the entry of a guilty or no contest plea.  The law has established certain well-defined standards to be applied in determining the validity of a conviction which resulted from a guilty or no contest plea.  Basically, any guilty or no contest plea must be made voluntarily and intelligently, with a knowledge of the fundamental constitutional rights involved and the direct penal consequences of the guilty plea, and the defendant’s expressed desire to waive his or her constitutional rights.[278]

            The law is clear that a defendant’s guilty plea is unconstitutional as involuntary and unintelligent where the defendant did not express an intelligent waiver of his or her fundamental constitutional rights unless the record demonstrates in the totality of the circumstances that the defendant was nevertheless aware of those rights.[279]

 

[278] Boykin v. Alabama, 395 U.S. 238 (1969); In re Tahl, 1 Cal.3d 122 (1969); People v. Howard, 1 Cal.4th 1132, 1174-1180 (1992).

[279] Boykin v. Alabama, 395 U.S. 238, 242-244 (1969); In re Tahl, 1 Cal.3d 122, 132 (1960); People v. Howard, 1 Cal.4th 1132, 1174-1180 (1992).

GROUNDS - INVALID PLEA - FOR UNPRESERVED RULE 11 ERRORS, DEFENDANT MUST SHOW HE WOULD NOT HAVE PLEADED GUILTY
United States v. Benitez, 124 S.Ct. 2333 (June 14, 2004) (to vacate plea on grounds of F.R.Crim.P. 11 errors [as distinguished from "structural errors" or fundamental constitutional errors under Boykin v. Alabama, to vacate the plea], and no objection was raised in trial court, defendant must establish reasonable probability that but for error, he would not have pleaded guilty).
http://laws.lp.findlaw.com/us/000/03167.html

POST CON - WAIVER OF RIGHTS BY IMMIGRANTS
Von Moltke v. Gillies, 332 U.S. 708 (1948) (court must make a thorough inquiry before accepting waiver of right to counsel). United States v. Mendez, 102 F.3d 126 (5th Cir. 1997) (waiver of right to jury trial by silence insufficient where defendant was unable to speak English and did not understand United States criminal system).

Lower Courts of Second Circuit

INVOLUNTARY PLEA CLAIM BASED ON MISINFORMATION CONCERNING IMMIGRATION CONSEQUENCES NOT BARRED
Zhang v. United States, ___ F.Supp.2d ___, 2005 WL 3086840 2005 U.S. Dist. LEXIS 28404 (E.D. N.Y. Nov. 18, 2005) (motion to vacate sentence pursuant to 28 U.S.C. 2255 on involuntary plea and ineffective counsel grounds for misadvice concerning immigration consequences not barred by failure to raise issues on direct appeal); Mandarino v. Ashcroft, 290 F. Supp.2d 253, 260-61 (D. Conn. 2002) (ignorance of deportation consequences of the defendant's sentence was "cause" for the defendant's failure to appeal the sentence); United States v. Singh, 305 F. Supp.2d 109, 111 (D.D.C. 2004) (permitting a procedurally barred 2255 claim regarding the voluntariness of a guilty plea made when the petitioner was not properly informed that deportation was absolute).

POST CON - FEDERAL - GROUNDS - INVOLUNTARY PLEA WHERE DEFENDANT TOLD ONLY CONVICTION "COULD" RESULT IN DEPORTATION WHERE IT WAS VIRTUALLY CERTAIN TO DO SO
Zhang v. United States, ___ F.Supp.2d ___, 2005 WL 3086840 2005 U.S. Dist. LEXIS 28404 (E.D. N.Y. Nov. 18, 2005) (vacating conviction through granting motion to vacate sentence pursuant to 28 U.S.C. 2255 on involuntary plea and ineffective counsel grounds for misadvice concerning immigration consequences where defendant was informed only that the conviction "could result in your deportation," where it was certain to do so).

POST CON RELIEF - GROUNDS - GENERAL TEST FOR VOLUNTARINESS OF PLEA - CONNECTICUT
State v. Aquino, ___ Conn. ___, 2005 Conn. App. LEXIS 226 (Conn. App. June 7, 2005) ("It is axiomatic that unless a plea of guilty is made knowingly and voluntarily, it has been obtained in violation of due process and is therefore voidable. . . . A plea of guilty is, in effect, a conviction, the equivalent of a guilty verdict by a jury. . . . In choosing to plead guilty, the defendant is waiving several constitutional rights, including his privilege against self- incrimination, his right to trial by jury, and his right to confront his accusers. . . . These considerations demand the utmost solicitude of which courts are capable [*13]  in canvassing the matter with the accused to make sure he has a full understanding of what the plea connotes and its consequences. . . . We therefore require the record affirmatively to disclose that the defendant's choice was made intelligently and voluntarily." (Citations omitted; internal quotation marks omitted.))

Ninth Circuit

POST CON RELIEF - FEDERAL - STANDARD OF REVIEW OF SUFFICIENCY OF PLEA COLLOQUY
United States v. Ross, 511 F.3d 1233, ___ (9th Cir. Jan. 14, 2008) ("We review de novo the sufficiency of a Rule 11 plea colloquy. United States v. King, 257 F.3d 1013, 1021 (9th Cir. 2001). A Rule 11 mistake not preserved by timely objection below is subject to plain error review. United States v. Dominguez Benitez, 542 U.S. 74, 76, 124 S.Ct. 2333, 159 L.Ed.2d 157 (2004). We review a district court's denial of a motion to withdraw a guilty plea for abuse of discretion. United States v. Davis, 428 F.3d 802, 805 (9th Cir. 2005).").

GUILTY PLEAS - FEDERAL - REFUSAL TO ACCEPT
In re Vasquez-Ramirez, 443 F.3d 692 (9th Cir. Apr. 6, 2006) (district judge may not reject a guilty plea that satisfies all requirements of FRCP 11(b); but may refuse to abide by plea agreement between defendant and the government; if plea agreement is rejected, judge must allow defendant to withdraw the plea; if defendant maintains the plea the court "may dispose of the case less favorably toward the defendant than the plea agreement contemplated. Fed. R. Crim. P. 11(c)(5)(C) . . . .").

POST CON RELIEF - FEDERAL - GROUNDS - INVALID PLEA - PREJUDICE STANDARD SAME AS FOR IAC
United States v. Monzon, 429 F.3d 1268 (9th Cir. Dec. 7, 2005) (conviction and sentence for possession of a firearm in furtherance of a drug trafficking crime reversed where the court committed plain error when it accepted guilty plea in violation of Federal Rule of Criminal Procedure 11, because court failed to establish a factual basis for believing that the defendant possessed the firearm at least partly for the purpose of protecting the drugs, where the defendant factually denied that intent during the plea colloquy, and the error affected defendants substantial rights, defined as a reasonable probability of a different outcome sufficient to undermine confidence in the outcome).
http://caselaw.lp.findlaw.com/data2/circs/9th/0330497p.pdf